WO2009028902A2 - Dérivé de complexe de métal organique et dispositifs émettant de la lumière organique l'utilisant - Google Patents

Dérivé de complexe de métal organique et dispositifs émettant de la lumière organique l'utilisant Download PDF

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WO2009028902A2
WO2009028902A2 PCT/KR2008/005084 KR2008005084W WO2009028902A2 WO 2009028902 A2 WO2009028902 A2 WO 2009028902A2 KR 2008005084 W KR2008005084 W KR 2008005084W WO 2009028902 A2 WO2009028902 A2 WO 2009028902A2
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group
substituted
deuterium
halogen
unsubstituted
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WO2009028902A3 (fr
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Dae-Woong Lee
Dong-Hoon Lee
Mun-Kyu Joo
Sang-Young Jeon
Jeung-Gon Kim
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LG Chem Ltd
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LG Chem Ltd
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Priority to US12/733,404 priority patent/US8431246B2/en
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Publication of WO2009028902A3 publication Critical patent/WO2009028902A3/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials

Definitions

  • the present invention relates to a novel organic metal complex derivative and an organic light emitting device using the same.
  • organic light emitting phenomenon refers to a phenomenon in which electric energy is converted to light energy by means of an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a structure usually comprising an anode, a cathode and an organic material layer interposed therebetween.
  • the organic material layer may be mostly formed in a multilayer structure comprising layers of different materials, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and the like, in order to improve efficiency and stability of the organic light emitting device.
  • the organic light emitting device having such a structure, when a voltage is applied between two electrodes, holes from the anode and electrons from a cathode are injected into the organic material layer, the holes and the electrons injected are combined together to form excitons. Further, when the excitons drop to a ground state, lights are emitted.
  • Such the organic light emitting device is known to have characteristics such as self-luminescence, high brightness, high efficiency, low drive voltage, wide viewing angle, high contrast, and high-speed response.
  • the materials used for the organic material layer of the organic light emitting device can be classified into a light emitting material and a charge transporting material, for example, a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material, according to their functions.
  • the light emitting material can be classified into a high molecular weight type and a low molecular weight type, according to their molecular weight, and divided into a fluorescent material from singlet excited states and a phosphorescent material from triplet excited states according to their light emitting mechanism. Further, the light emitting material can be classified into a blue, green, or red light emitting material and a yellow or orange light emitting material required for giving more natural color, according to a light emitting color.
  • an efficiency of a device is lowered owing to maximum luminescence wavelength moved to a longer wavelength due to the interaction between the molecules, the deterioration of color purity and the reduction in light emitting efficiency when only one material is used for the light emitting material, and therefore a host/dopant system can be used as the light emitting material for the purpose of enhancing the color purity and the light emitting efficiency through energy transfer. It is based on the principle that if a small amount of a dopant having a smaller energy band gap than a host which forms a light emitting layer, excitons which are generated in the light emitting layer are transported to the dopant, thus emitting a light having a high efficiency.
  • a material constituting the organic material layer in the device for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, and an electron injecting material should be essentially composed of a stable and efficient material.
  • a stable and efficient organic material layer material for the organic light emitting device has not yet been fully realized. Accordingly, the development of new materials is continuously desired. The development of such a material is equally required to the above-mentioned other organic electronic devices.
  • the present inventors have synthesized an organic metal complex derivative having a novel structure, and they found that the derivative exhibits the effect of reducing voltage in an organic light emitting device.
  • the present invention provides an organic metal complex derivative represented by the following Formula 1 or 2. [Formula 1]
  • Y is a ligand having a unsubstituted or substituted hydroxyaryl-N-hetero ring, and is any one selected from the group consisting of a ligand containing 8-hydroxy-2-methylquinoline, a bidentate Schiff base ligand, and a tetradentate Schiff base ligand, n is 1 or 2, M is a metal having an oxidation number of +2, +3 or +4,
  • X Deutrium or Fluorine
  • m 1 to 5
  • O oxygen
  • A is formed in that it is substituted with oxygen and a benzene group which is substituted with the X, wherein the A may be selected from the group consisting of a C 3 -C 4O cycloalkylene group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a C 1 -C 4O alkyl group, a C 2 -C 40 alkenyl group, a C 1 -C 40 alkoxy group, a C 3 -C 4 O cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 40 heteroaryl group; a C 2 -C 40 heterocycloalkylene group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a
  • Y is a ligand having a unsubstituted or substituted hydroxyaryl-N-hetero ring, and is any one selected from the group consisting of a ligand containing 8-hydroxy-2-methylquinoline, a bidentate Schiff base ligand, and a tetradentate Schiff base ligand, n is 1 or 2,
  • M is a metal having an oxidation number of +2, +3 or +4,
  • Ll is Xm wherein X is Deutrium or Fluorine, m is 1 to 4 O is oxygen,
  • a and A' are each independently the same as or different from each other, and the same as defined in the A in the Formula 1
  • the present invention provides an organic electronic device comprising a first electrode, a second electrode, and one or more organic material layers disposed therebetween, wherein at least one layer of the organic material layers comprises the organic metal complex derivative.
  • the present invention provides an organic light emitting device having a forward or reverse structure, prepared by sequentially depositing an anode, one or more organic material layers, and a cathode on a substrate, wherein at least one layer of the organic material layers comprises the organic metal complex derivative.
  • FIG. 1 is a IH-NMR graph of an entire structure according to Formula 1-1 of the present invention.
  • FIG. 2 is a IH-NMR graph of an aryl group in which deuterium of Formula 1-1 of the present invention is substituted.
  • FIGs. 3 to 7 are cross-sectional views illustrating the structure of the organic light emitting device according to the present invention. [Numeral References]
  • the hydroxyaryl-N-hetero ring includes a hetero ring containing at least one nitrogen and an aryl group containing at least one hydroxyl group, in which oxygen of the hydroxyl group and nitrogen of the hetero ring may be coordinately bonded to a metal in the form of pentagon to heptagon.
  • the hetero ring containing at least one nitrogen and the aryl group containing at least one hydroxyl group may be linked by a direct bond, or form an aliphatic, aromatic, heteroaliphatic, or heteroaromatic condensed ring or a spiro bond, together with the adjacent group.
  • the substituted hydroxyaryl-N-hetero ring may be substituted with one or more selected from the group consisting of hydrogen; deuterium; a Cj-C 40 alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a Ci-C 40 alkoxy group, a C 3 -C 40 cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 40 heteroaryl group; a C 3 -C 40 cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a
  • Y of Formula 1 or 2 is preferably a ligand containing 8-hydroxy-2-methylquinoline represented by the following Formula 3 as a ligand having a substituted or unsubstituted hydroxyaryl-N-hetero ring.
  • Rl to R6 are the same as or different from each other, and may be selected from the group consisting of a C 1 -C 40 alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a Cj-C 4O alkyl group, a C 2 -C 40 alkenyl group, a C 1 -C 40 alkoxy group, a C 3 -C 4 O cycloalkyl group, a C 2 -C 4O heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 40 heteroaryl group; a C 3 -C 4O cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a Cj-C
  • the tetradentate Schiff base ligand is preferably a compound represented by the following Formula 4.
  • R7 to RlO are the same as or different from each other, and may be selected from the group consisting of a C 1 -C 40 alkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a C 1 -C 4 O alkyl group, a C 2 -C 4O alkenyl group, a C 1 -C 4O alkoxy group, a C 3 -C 40 cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 40 heteroaryl group; a C 3 -C 40 cycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a
  • C 1 -C 40 alkyl group a C 2 -C 40 alkenyl group, a Ci ⁇ C 40 alkoxy group, a C 3 -C 40 cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 40 heteroaryl group; a C 2 -C 40 heterocycloalkyl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, an amino group, a nitrile group, a nitro group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a Ci-C 40 alkoxy group, a C 3 -C 4O cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 4O heteroaryl group;
  • the tetradentate Schiff base ligand is preferably a compound represented by the following Formula 5.
  • R7 to R9 and R7' to R9' are the same as defined in R7 to R9 of Formula 4
  • E is formed in that it functions as a bridge connecting nitrogen on both sides wherein the E, specifically, may be selected from the group consisting of a C 1 -C 40 alkylene group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, a nitrile group, a nitro group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 1 -C 40 alkoxy group, a C 3 -C 40 cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 40 aryl group and a C 5 -C 40 heteroaryl group; a C 3 -C 40 cycloalkylene group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, a nitrile group, a nitro group, a Ci ⁇ C 40 alkyl group,
  • M is a metal having an oxidation number of 2 to 4, and may preferably include aluminum, zinc, zirconium, iridium, lithium, gallium, molybdenum or the like.
  • aryl group may be substituted with deuterium, -CN, -SiR 3 , -CF 3 or the like.
  • the organic metal complex derivative M represented by Formula 1 and 2 according to the present invention is aluminum;
  • A is a C 6 -C 40 aryl group unsubstituted or substituted with one or more groups selected from the group consisting of halogen, deuterium, a nitrile group, a nitro group, a C 1 -C 40 alkyl group, a C 2 -C 40 alkenyl group, a C 1 -C 4 O alkoxy group, a C 3 -C 40 cycloalkyl group, a C 2 -C 40 heterocycloalkyl group, a C 6 -C 4 O aryl group and a C 5 ⁇ C 40 heteroaryl group;
  • B is a compound represented by Formula 2, wherein X is -S-; C is a C 6 -C 40 aryl group unsubstitute
  • organic metal complex derivative represented by Formula 1 or 2 according to the present invention is selected from the group consisting of the following Table 1 to 2, but are not limited thereto. [Table 1]
  • the compound represented by Formula 1 or 2 of the present invention can be used due to its structural property as an organic material layer in an organic electronic device and organic light emitting device.
  • the organic metal complex derivative according to the present invention can be applied to the organic light emitting device by a typical preparation method of organic light emitting device.
  • the organic light emitting device has a structure comprising a first electrode, a second electrode, and organic material layers disposed therebetween, and can be prepared by using typical method and materials, except for using the organic metal complex derivative according to the present invention as the organic material layer of organic light emitting device.
  • the structure of the organic light emitting device according to the present invention is illustrated in FIGs. 2 to 6.
  • the organic light emitting device can be prepared by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate using a PVD (physical vapor deposition) process such as sputtering and e-beam evaporation to form an anode; forming an organic material layer comprising a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode; and depositing a material, which can be used as a cathode, thereon.
  • PVD physical vapor deposition
  • the organic light emitting device can be prepared by sequentially depositing a cathode material, an organic matter layer, and an anode mater in sequence on a substrate (International Laid-Open Publication WO2003/012890).
  • the organic matter layer may be a multi-layer structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, etc., but is not limited thereto.
  • the organic matter layer may be a single layer structure.
  • the organic matter layer can be prepared in a very small number of layers by a solvent process, not by a deposition, for example, spin coating, deep coating, doctor blade, screen printing, inkjet printing, thermal transfer using various polymer materials.
  • the anode material is preferably a material having a large work function to facilitate hole injection usually to an organic material layer.
  • the cathode material is preferably a material having a small work function to facilitate electron injection usually to an organic material layer.
  • the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or an alloy thereof; multilayer structure materials such as LiF/Al and LiO 2 /Al, but not limited thereto.
  • the following materials can be used for a hole injecting material, a hole transporting material, a light emitting material, and electron transporting material.
  • the hole injecting material is a material facilitating hole injection from an anode at low voltage.
  • the HOMO (highest occupied molecular orbital) level of the hole injecting material is preferably located between the work function of the anode materials and the HOMO level of its neighboring organic material layer.
  • the hole injecting material examples include organic materials of metal porphyrin, oligothiophene, and arylamine series, organic materials of hexanitrile hexaazatriphenylene and quinacridone series, organic materials of perylene series, and conductive polymers of anthraquinone, polyaniline, and polythiophene series, but are not limited thereto.
  • the hole transporting material is preferably a material having high hole mobility, which can transfer holes from the anode or the hole injecting layer toward the light emitting layer.
  • Specific examples thereof include organic materials of arylamine series, conductive polymers, and block copolymers having both conjugated portions and non-conjugated portions, but are not limited thereto.
  • the light emitting material are a material capable of emitting visible light by accepting and recombining holes from the hole transporting layer and electrons from the electron transporting layer, preferably a material having high quantum efficiency for fluorescence and phosphorescence. Specific examples thereof include
  • AIq 3 8-hydroxyquinoline aluminum complex
  • the electron transporting material is suitably a material having high electron mobility, which can transfer electrons from the cathode to the light emitting layer.
  • a material having high electron mobility which can transfer electrons from the cathode to the light emitting layer.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (AIq 3 ); complexes including AIq 3 ; organic radical compounds; and hydroxyflavone-metal complexes, but are not limited thereto.
  • the organic light emitting device according to the invention may be of a front-side, backside or double-sided light emission according to the materials used.
  • the compound according to the invention can function in an organic electronic device including an organic solar cell, an organic photoconductor, and an organic transistor, according to a principle similar to that applied to the organic light emitting device.
  • a ligand 2 was obtained in the same manner as in the preparation method of ligand 1, except for using the compound A instead of 4-hydroxyphenylboronic acid.
  • a ligand 5 was obtained in the same manner as in the preparation method of ligand 1, except for using bromopentafiuorobenzene instead of bromobenzene-d5, and xylene instead of tetrahydrofuran
  • Example 1 was dissolved in anhydrous toluene or anhydrous tetrahydrofuran, and then slowly added thereto, followed by stirring under heating for 1 to 4 hrs. Then, temperature was reduced to room temperature to produce the precipitate. Ethanol was added thereto, and then the precipitate was filtered. The filtered solid was recrystallized using dichloromethane or toluene and ethanol, and then dried under vacuum to obtain an aluminum complex. The aluminum complex was analyzed by NMR and MS analysis.
  • An aluminum complex compound of Formula 1-4 was obtained in the same manners as in Example 1, except for using the ligand 2 prepared in Preparation Example 2 instead of the ligand 1 of Example 1.
  • the aluminum complex was analyzed by NMR and MS analysis.
  • An aluminum complex compound of Formula 1-60 was obtained in the same manners as in Example 1, except for using the ligand 3 prepared in Preparation Example 3 instead of the ligand 1 of Example 1.
  • An aluminum complex compound of Formula 2-1 was obtained in the same manners as in Example 1, except for using the ligand 4 (0.5 equivalent) prepared in Preparation Example 4 instead of the ligand 1 of Example 1.
  • An aluminum complex compound of Formula 1-74 was obtained in the same manners as in Example 1, except for using the ligand 5 prepared in Preparation Example 3 instead of the ligand 1 of Example 1.
  • HAT hexanitrile hexaazatriphenylene
  • NPB 4,4 '-bis [N-(I -naphthyl)-N-phenylamino] biphenyl
  • an aluminum complex represented by Formula 1-1 was doped with Btp2Ir(acac) (4%), and vacuum-deposited to form a red light emitting layer (300 A). [Btp2Ir(acac)]
  • AIq 3 was sequentially vacuum-deposited to a thickness of 200 A, thus to form an electron transporting layer.
  • lithium fluoride (LiF) and aluminum were sequentially vacuum-deposited to a thickness of 12 A and 2000 A, respectively.
  • a cathode was formed to prepare an organic light emitting device.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A/sec and the deposition rates of lithium fluoride and aluminum of the cathode were maintained at 0.3 A/sec and 2 A/sec, respectively.
  • the vacuum degree during deposition was maintained at 2 x 10 ' ⁇ 5 x 10 " torr.
  • NPB 4,4'-bis[N-(l-naphthyl)-N-phenylamino] biphenyl (NPB) (400 A), a red light emitting layer (300 A)formed by doping and vacuum-depositing Btp2Ir(acac) (4%) into Formula 1-34, a compound of Alq3 (200 A) were sequentially coated by thermal vacuum deposition to form a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting, respectively.
  • lithium fluoride (LiF) and aluminum were sequentially vacuum-deposited to a thickness of 12 A and 2000 A, respectively.
  • a cathode was formed to prepare an organic light emitting device.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A/sec and the deposition rates of lithium fluoride and aluminum of the cathode were maintained at 0.3 A/sec and 2 A/sec, respectively.
  • the vacuum degree during deposition was maintained at 2 x 10 "7 ⁇ 5 x 10 "8 torr.
  • a glass substrate (Corning 7059 glass) on which a thin film of ITO (indium tin oxide) was coated to a thickness of 1000 A was immersed in distilled water containing a detergent to wash the substrate with ultrasonic waves.
  • the detergent was a product commercially available from Fisher Co. and the distilled water has been filtered previously by using a filter commercially available from Millipore Co.
  • ITO was washed for 30 minutes, and then washing with ultrasonic waves was repeated twice for 10 minutes by using distilled water. After the completion of washing with distilled water, washing with ultrasonic waves was carried out by using solvents such as isopropyl alcohol, acetone and methanol.
  • NPB 4,4'-bis[N-(l-naphthyl)-N-phenylamino] biphenyl (NPB) (400 A), the following CBP compound doped with 4% Btp2Ir(acac) (300 A), and Alq3 (200 A) were sequentially coated by thermal vacuum deposition to form a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer, respectively.
  • lithium fluoride (LiF) and aluminum were sequentially vacuum-deposited to a thickness of 12 A and 2000 A, respectively.
  • a cathode was formed to prepare an organic light emitting device.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A/sec and the deposition rates of lithium fluoride and aluminum of the cathode were maintained at 0.3 A/sec and 2 A/sec, respectively.
  • the vacuum degree during deposition was maintained at 2 x 10 "7 ⁇ 5 x 10 "8 torr.

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Abstract

La présente invention porte sur un nouveau dérivé de complexe de métal organique et sur un dispositif émettant de la lumière organique le comportant.
PCT/KR2008/005084 2007-08-31 2008-08-29 Dérivé de complexe de métal organique et dispositifs émettant de la lumière organique l'utilisant Ceased WO2009028902A2 (fr)

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US12/733,404 US8431246B2 (en) 2007-08-31 2008-08-29 Organic metal complexs derivative and organic light emitting device using the same

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KR20090022814A (ko) 2009-03-04
US20100171116A1 (en) 2010-07-08
US8431246B2 (en) 2013-04-30
JP5432147B2 (ja) 2014-03-05
JP2010537975A (ja) 2010-12-09
KR100963378B1 (ko) 2010-06-14

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